S_N2′ Addition of Organometallic Reagents to β′-Amino Cyclohexenyl Sulfone Derivatives

Y. Pan Department of Chemistry, Purdue University, West Lafayette, IN, 47907

S. A. Hardinger Department of Chemistry, Purdue University, West Lafayette, IN, 47907

P. L. Fuchs Department of Chemistry, Purdue University, West Lafayette, IN, 47907

Abstract

Organolithium reagents add to cyclohexenyl sulfone 12 to provide β-amino sulfones that can be eliminated to afford cis- adducts 17a-c. Cuprate reagents undergo trans addition to cyclohexenyl ammonium salt 13 to generate the isomeric vinyl sulfones 18a-c. This stereochemistry is opposite to what had been previously observed in cyclopentenyl derivatives; mechanistic rationale is provided.

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S_N2′ Addition of Organometallic Reagents to β′-Amino Cyclohexenyl Sulfone Derivatives

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SN2′ Addition of Organometallic Reagents to β′-Amino Cyclohexenyl Sulfone Derivatives

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S_N2′ Addition of Organometallic Reagents to β′-Amino Cyclohexenyl Sulfone Derivatives